Total Synthesis of Aphadilactones A-D

被引：15

作者：

Yin, Jian-Peng ^{[1
]}

Gu, Min ^{[2
]}

Li, Ying ^{[1
]}

Nan, Fa-Jun ^{[2
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Natl Ctr Drug Screening, Shanghai 201203, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 13期

基金：

中国国家自然科学基金;

关键词：

DIELS-ALDER REACTIONS; BIOLOGICAL EVALUATION;

D O I：

10.1021/jo501117k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of aphadilactones A-D, diastereomeric natural products recently isolated from the Meliaceae plant Aphanamixis grandifolia by Yue and co-workers, which possess an unprecedented carbon skeleton, has been achieved. The synthesis features a catalytic asymmetric hetero-Diels-Alder reaction to form the dihydropyran ring, concurrent installation of the lactone and furan moieties via a tandem acid-catalyzed acetal cleavage, oxidation, and cyclization process, and an intermolecular Diels-Alder reaction to forge the target products.

引用

页码：6294 / 6301

页数：8

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